HCID 10202989, compound → HCID 68420335, compound

HRID 2374802Notes

Reaction equation

HRID 2374802 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:32])[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:33].O1CCOCC1>O1CCOCC1>[ClH:33].[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6](=[C:16]3[CH2:17][CH2:18][N:19]([C:22](=[O:32])[CH2:23][NH2:24])[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 10202989HCID 10202989, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 68420335HCID 68420335, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.40 g (3.25 mmol) of t-butyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethylcarbamate was dissolved in 20 ml of 1,4-dioxane. 12 ml of 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution, and they were stirred overnight. After the neutralization with 4 N aqueous sodium hydroxide solution, the solvent was evaporated under reduced pressure. Saturated aqueous sodium chloride solution was added to the reaction mixture. After the extraction with ethyl acetate 3 times, the extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. 10 ml of a solution of ethyl acetate:hexane (1:2) and then 2 ml of 4 N hydrochloric acid/1,4-dioxane solution were added to the residue. The resultant precipitates were taken by the filtration, washed with a solution of ethyl acetate:hexane (1:2) and air-dried. After further drying under reduced pressure, the title compound was obtained.

Workup

  1. customAfter the neutralization with 4 N aqueous sodium hydroxide solution, the solvent was evaporated under reduced pressure
  2. additionSaturated aqueous sodium chloride solution was added to the reaction mixture
  3. extractionAfter the extraction with ethyl acetate 3 times
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. addition10 ml of a solution of ethyl acetate:hexane (1:2) and then 2 ml of 4 N hydrochloric acid/1,4-dioxane solution were added to the residue
  7. customThe resultant precipitates
  8. filtrationwere taken by the filtration
  9. washwashed with a solution of ethyl acetate:hexane (1:2)
  10. customair-dried
  11. customAfter further drying under reduced pressure

Sources & evidence

ORD record
ord-a6199737e85a4dfbb304f9bd4354efdb
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

Loading…